Effective Work Sample Exercises for Hiring a Chief Technology Officer

The Chief Technology Officer (CTO) role is pivotal to an organization's success in today's technology-driven business landscape. As the senior executive responsible for technological vision and strategy, a CTO must possess a unique blend of technical expertise, leadership skills, strategic thinking, and business acumen. Traditional interviews often fail to reveal whether candidates can truly perform in these multifaceted areas.

Work samples and role plays provide a window into how candidates actually approach real-world challenges they'll face as CTOs. By observing candidates in action—developing strategies, making technical decisions, managing teams, and communicating complex concepts—hiring teams can gain invaluable insights that interviews alone cannot provide.

For a C-suite position like CTO, the cost of a poor hiring decision is extraordinarily high. Beyond the immediate financial impact, a misaligned technology leader can derail digital transformation initiatives, damage team morale, and create technical debt that hampers the organization for years. Well-designed work samples help mitigate this risk by revealing how candidates think, lead, and execute under conditions that simulate actual job responsibilities.

The following exercises are specifically designed to evaluate the essential competencies of an effective CTO: strategic thinking, innovative problem-solving, collaboration, talent management, and business acumen. Each exercise presents candidates with realistic scenarios they would encounter in the role, allowing you to assess their capabilities in context rather than through hypothetical discussions.

By incorporating these exercises into your hiring process, you'll be able to differentiate between candidates who can talk about technology leadership and those who can actually deliver it. This approach not only helps identify the most qualified candidates but also demonstrates to top talent that your organization values rigorous, fair assessment and is serious about finding the right technology leader.

Activity #1: Technology Strategy Alignment Exercise

This exercise evaluates a candidate's ability to develop a technology strategy that aligns with business objectives—a fundamental responsibility of any CTO. It assesses strategic thinking, business acumen, and the ability to translate technical possibilities into business value. The exercise reveals how candidates approach long-term planning while balancing innovation with practical constraints.

Directions for the Company:

• Prepare a brief (1-2 page) document outlining your company's business strategy, current technology landscape, and key challenges. Include information about market position, growth targets, and competitive pressures.
• Create a simplified version of your current technology stack and architecture diagram.
• Develop a list of 3-4 business objectives that technology needs to support (e.g., scaling for growth, improving customer experience, reducing operational costs).
• Send these materials to the candidate 48 hours before the interview.
• Allocate 30 minutes for the candidate's presentation and 15 minutes for questions and feedback.
• Ensure the CEO or another C-suite executive participates alongside technical leaders to evaluate business alignment.

Directions for the Candidate:

• Review the provided materials and develop a 12-month technology roadmap that supports the company's business objectives.
• Prepare a 20-minute presentation that includes:
• Your assessment of the current technology landscape's strengths and weaknesses
• Proposed strategic technology initiatives with clear business value
• High-level implementation approach and resource requirements
• Key risks and mitigation strategies
• Success metrics for measuring impact
• Be prepared to explain your prioritization decisions and how they align with business goals.
• Your presentation should be strategic but demonstrate technical depth where relevant.

Feedback Mechanism:

• After the presentation, interviewers should provide specific feedback on one aspect the candidate handled exceptionally well (e.g., "Your approach to balancing innovation with practical implementation was particularly strong").
• Interviewers should also provide one area for improvement (e.g., "We'd like to see more consideration of how these initiatives would impact our existing team structure").
• Give the candidate 5-10 minutes to respond to the improvement feedback and adjust their approach or explain how they would incorporate this feedback.

Activity #2: Technical Crisis Management Simulation

This exercise evaluates how candidates handle high-pressure technical situations that require both leadership and technical expertise. It reveals decision-making abilities under stress, technical problem-solving skills, and communication effectiveness during crisis scenarios—all critical for a CTO who must ultimately be responsible for system reliability and security.

Directions for the Company:

• Create a detailed scenario of a significant technical crisis (e.g., major security breach, critical system outage affecting customers, data loss incident).
• Prepare background information including system architecture diagrams, relevant logs, and initial incident reports.
• Assemble a panel of 2-3 people who will role-play as members of the technical team during the crisis.
• The simulation should last 45 minutes: 5 minutes for briefing, 30 minutes for the simulation, and 10 minutes for debrief and feedback.
• Brief the role players on how to respond to different approaches the candidate might take.

Directions for the Candidate:

• You will be presented with a technical crisis scenario that requires immediate attention.
• As the CTO, you will lead a response team (played by the interview panel) to:
• Assess the situation and gather critical information
• Develop and implement a plan to address the immediate crisis
• Make decisions about resource allocation and prioritization
• Determine communication strategy for stakeholders (executives, customers, team)
• Begin planning for long-term prevention of similar incidents
• You should demonstrate both technical understanding and leadership throughout the exercise.
• Focus on clear communication, decisive action, and strategic thinking even under pressure.

Feedback Mechanism:

• After the simulation, provide feedback on what the candidate handled well (e.g., "Your ability to quickly identify the root cause while keeping the team focused was impressive").
• Offer one specific area for improvement (e.g., "Your communication with non-technical stakeholders could be more concise and less technical").
• Ask the candidate to draft a brief follow-up communication to the executive team about the incident, incorporating the feedback provided.

Activity #3: Technology Investment Prioritization Exercise

This exercise assesses a candidate's ability to make strategic technology investment decisions with limited resources—a core responsibility for CTOs who must manage technology budgets effectively. It reveals how candidates evaluate competing priorities, balance short-term needs with long-term vision, and make data-driven decisions aligned with business objectives.

Directions for the Company:

• Create a scenario with a fixed technology budget (e.g., $2 million) and a list of 7-10 potential technology initiatives with varying costs, benefits, risks, and timeframes.
• For each initiative, provide a brief description, estimated cost, potential business impact, implementation timeline, and dependencies.
• Include a mix of infrastructure improvements, new capabilities, technical debt reduction, and innovation projects.
• Prepare information about current pain points and business priorities to provide context.
• Allow 45 minutes for this exercise: 10 minutes for review, 25 minutes for analysis and decision-making, and 10 minutes for presentation and feedback.

Directions for the Candidate:

• Review the list of potential technology initiatives and the fixed budget constraint.
• Develop an investment plan that allocates the budget across initiatives to maximize business value.
• Create a simple presentation (can be on whiteboard or paper) that includes:
• Your selected initiatives and budget allocation
• Rationale for your prioritization decisions
• Expected outcomes and business impact
• Initiatives you chose not to fund and why
• Approach to measuring ROI and adjusting course if needed
• Be prepared to explain how your investment strategy aligns with both short-term needs and long-term technology vision.

Feedback Mechanism:

• Provide feedback on a strength in the candidate's approach (e.g., "Your consideration of dependencies between projects showed excellent systems thinking").
• Offer constructive feedback on an area to improve (e.g., "We'd like to see more emphasis on quantifying the expected business outcomes").
• Ask the candidate to reconsider one specific decision based on the feedback and explain how they would adjust their approach.

Activity #4: Engineering Leadership Role Play

This exercise evaluates a candidate's ability to lead and develop technical teams—a critical function for CTOs who must build high-performing engineering organizations. It assesses talent management skills, leadership approach, and ability to balance technical guidance with empowerment of team members.

Directions for the Company:

• Create a scenario involving a challenging team situation, such as:
• A talented but difficult engineer who is creating team friction
• A team struggling with delivery timelines and quality issues
• A technical disagreement between team members about architecture approach
• A team resistant to adopting new methodologies or technologies
• Prepare a brief on the team composition, individual backgrounds, and relevant history.
• Select an experienced engineering leader to role-play as the team member(s).
• Allow 30 minutes for the role play and 15 minutes for discussion and feedback.
• Provide the scenario to the candidate 30 minutes before the exercise.

Directions for the Candidate:

• Review the team scenario provided and prepare for a one-on-one meeting with a key team member (or team meeting, depending on the scenario).
• Your objective is to address the situation effectively while demonstrating your leadership approach.
• During the role play, focus on:
• Understanding the underlying issues through effective questioning
• Providing clear guidance and expectations
• Balancing technical direction with team empowerment
• Demonstrating empathy while maintaining accountability
• Working toward concrete next steps and solutions
• Be prepared to explain your leadership philosophy and how it informed your approach to this situation.

Feedback Mechanism:

• After the role play, provide feedback on what the candidate did particularly well (e.g., "Your ability to uncover the root cause through thoughtful questions was excellent").
• Offer one specific area for improvement (e.g., "You could have been more explicit about performance expectations and consequences").
• Ask the candidate to reflect on the feedback and describe how they would approach the follow-up meeting with this team member, incorporating the feedback provided.

Frequently Asked Questions

How long should we allocate for these work sample exercises?

Each exercise requires approximately 45-60 minutes, including preparation, execution, and feedback. We recommend conducting no more than two exercises in a single day to avoid candidate fatigue. The Technology Strategy Alignment Exercise works well as a take-home assignment with an in-person presentation, while the other exercises are best conducted on-site.

Should we use all four exercises for every CTO candidate?

Not necessarily. Select the exercises most relevant to your organization's needs and challenges. For a startup focused on rapid growth, the Technology Strategy and Investment Prioritization exercises might be most valuable. For an established company with large engineering teams, the Engineering Leadership Role Play might be critical. Always ensure your process respects candidates' time while providing sufficient data for decision-making.

How should we evaluate candidates across multiple exercises?

Create a structured scorecard for each exercise that maps to the key competencies for your CTO role. Have multiple evaluators score independently before discussing. Look for patterns across exercises—strong candidates should demonstrate consistent capabilities in strategic thinking, technical depth, leadership, and communication across different scenarios.

What if a candidate pushes back on participating in these exercises?

Explain the value of work samples in making fair, objective hiring decisions and how they benefit both parties. Be willing to accommodate reasonable concerns about time commitment or confidentiality. For senior candidates with extensive track records, you might consider reducing the scope or number of exercises, but some form of work sample is valuable even for experienced executives.

How can we ensure these exercises don't disadvantage candidates from underrepresented groups?

Design exercises that minimize bias by focusing on job-relevant skills rather than cultural fit. Provide clear instructions and equal preparation time to all candidates. Use structured evaluation criteria established in advance. Have diverse interview panels evaluate the exercises. Be conscious of and mitigate potential bias in feedback delivery.

Should we compensate candidates for their time spent on these exercises?

For extensive take-home assignments like the Technology Strategy Exercise, consider offering compensation, especially if it requires more than 2-3 hours of preparation. This demonstrates respect for candidates' time and expertise while potentially increasing participation rates among passive candidates who might otherwise decline.

Hiring the right CTO is one of the most consequential decisions an organization can make. The technology leader you select will shape not only your technical capabilities but also your innovation culture, digital transformation journey, and ultimately your competitive position. By incorporating these work sample exercises into your hiring process, you gain invaluable insights into how candidates actually think and operate in realistic scenarios.

Remember that these exercises serve a dual purpose: they help you evaluate candidates more effectively, and they demonstrate to top talent that your organization takes a thoughtful, rigorous approach to hiring. The best CTO candidates will appreciate a process that allows them to showcase their actual capabilities rather than just discuss them.

For more resources to enhance your hiring process, check out Yardstick's AI Job Description Generator, AI Interview Question Generator, and AI Interview Guide Generator. You can also find more information about the CTO role in our Chief Technology Officer job description.

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